Q.Oxidation of ketones involves carbon-carbon bond cleavage. Name the product(s) formed on oxidising 2,5-dimethylhexan-3-one using a strong oxidising agent.

Step 1. 2,5-Dimethylhexan-3-one is (CH3)2CH-CO-CH2-CH(CH3)-CH3 -- its carbonyl carbon (C3) is flanked on one side by an isopropyl group (C1, C2, and the 2-methyl substituent -- 3 carbons total) and on the other by a 4-carbon isobutyl-type fragment (C4, C5, C6, and the 5-methyl substituent).

Step 2. Popoff's rule (Section 12.5.B.2) states that oxidative C-C cleavage places the resulting -COOH (built from the original carbonyl carbon) with the SMALLER flanking alkyl group -- so the carbonyl carbon (C3) combines with the isopropyl side (C1-C2 fragment) to give (CH3)2CH-COOH, isobutyric acid.

Step 3. On the LARGER side, the carbon directly bonded to the original carbonyl (C4) becomes its OWN new -COOH carbon (exactly as the book's own pentan-2-one example shows the propyl fragment's own first carbon becoming propanoic acid's carboxyl carbon) -- giving HOOC-CH(CH3)-CH3 from the C4-C5(with its methyl)-C6 fragment, which is ALSO isobutyric acid, (CH3)2CH-COOH. …

Draw out the full structure of 2,5-dimethylhexan-3-one explicitly (numbering C1-C6 plus both methyl substituents), identify the smaller and larger alkyl fragments flanking the carbonyl, then apply Po …

• Assuming the two cleavage products must be different acids just because the two flanking alkyl fragments have different raw carbon counts (3 versus 4) before cleavage -- once the carbonyl carbon itself is added to the smaller side, and the …